US6646121B2 - Sucralose composition and process for its preparation - Google Patents

Sucralose composition and process for its preparation Download PDF

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Publication number
US6646121B2
US6646121B2 US09/991,123 US99112301A US6646121B2 US 6646121 B2 US6646121 B2 US 6646121B2 US 99112301 A US99112301 A US 99112301A US 6646121 B2 US6646121 B2 US 6646121B2
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Prior art keywords
sucralose
stability
moisture
crystallization
solution
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US09/991,123
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US20020120134A1 (en
Inventor
Fiesal El Kabbani
Amal Brohmi
Christian Heiss
Juan Navia
Steven J. Catani
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Tate and Lyle Technology Ltd
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McNeil PPC Inc
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Priority to US09/991,123 priority Critical patent/US6646121B2/en
Application filed by McNeil PPC Inc filed Critical McNeil PPC Inc
Assigned to MCNEIL-PPC, INC. reassignment MCNEIL-PPC, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BROHMI, AMAL, KABBANI, FIESAL EL, NAVIA, JUAN, CATANI, STEVEN J., HEISS, CHRISTIAN
Publication of US20020120134A1 publication Critical patent/US20020120134A1/en
Priority to US10/632,876 priority patent/US6809198B2/en
Publication of US6646121B2 publication Critical patent/US6646121B2/en
Application granted granted Critical
Priority to US10/919,656 priority patent/US20050013922A1/en
Assigned to TATE & LYLE PUBLIC LIMITED COMPANY reassignment TATE & LYLE PUBLIC LIMITED COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MCNEIL-PPC, INC.
Priority to US11/522,566 priority patent/US8017767B2/en
Assigned to TATE & LYLE TECHNOLOGY LIMITED reassignment TATE & LYLE TECHNOLOGY LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TATE & LYLE PUBLIC LIMITED COMPANY
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification

Definitions

  • the invention relates to an improved form of sucralose and a process for making it.
  • Sucralose (4,1′,6′-trichloro-4,1′,6′-trideoxy-galactosucrose) a high intensity sweetener made from sucrose, can be used in many food and beverage applications.
  • Sucralose unlike many artificial sweeteners, can be used in cooking and baking with no loss of sweetening power.
  • Sucralose is generally made following the procedures set forth in U.S. Pat. Nos. 4,362,869; 4,380,476; 4,801,700; 4,950,746; 5,470,969 and 5,498,709. In all these procedures one of the final steps in the synthesis is a deacylation followed by the crystallization of the sucralose. Laboratory scale methods for crystallizing sucralose have been described in U.S. Pat. Nos. 4,343,934; 5,141,860; 4,977,254; 4,783,526; 4,380,476; 5,298,611; 4,362,869; 4,801,700; and 4,980,463.
  • the deacylation of the sucralose precursor is performed in methanol with a catalytic amount of sodium methoxide.
  • the resulting sucralose solution is contacted with an ion exchange resin to convert the residual sodium methoxide to methanol.
  • the ion exchange resin is then removed and the volatile solvents and reaction byproducts are removed by co-distillation with water, which results in a solvent switch to water.
  • the mixture is decolorized by contacting with activated carbon.
  • the carbon is removed to provide a decolorized sucralose solution suitable for crystallizing sucralose.
  • the sucralose solution is concentrated to about 55 weight percent sucralose (at about 50° C.).
  • the crystallization is performed by reducing the temperature to about 22° C. and adding of about 2 percent sucralose seed crystals.
  • the crystals that formed are separated from the mother liquor by centrifugation then dried.
  • the mother liquor that is separated from the crystals is added to the next batch just prior to decolorization.
  • crystalline sucralose with residual moisture content of from about 0.5 to about 10 percent by weight has improved stability.
  • a product comprising crystalline sucralose in a container that will maintain the moisture content.
  • the container will have moisture vapor transfer rate (MVTR) of not more than 0.25 gram water/100 square inches of surface area/24 hours, when tested at 38° C. at 92 percent relative humidity.
  • MVTR moisture vapor transfer rate
  • FIG. 1 is a flow chart of one embodiment of the crystallization process described herein.
  • an aqueous sucralose containing reaction mixture is contacted with the mother liquor and then transferred to the decolorizing tank.
  • the mixture is then filtered and concentrated.
  • the concentrated sucralose containing solution is transferred to a crystallizer, seeded, cooled and the crystals of sucralose are separated from the mother liquor by centrifugation.
  • the sucralose crystals are then dried and packaged. The mother liquor is recycled to the beginning of this process.
  • Sucralose and the methods of making sucralose have been described in numerous patents such as U.S. Pat. Nos. 4,801,700; 4,950,746; 5,470,969 and 5,498,709 which are hereby incorporated herein by reference.
  • the reaction mixture containing the sucralose needs to be neutralized, stabilized, decolorized and the sucralose removed from the mixture by crystallization.
  • the reaction mixture containing the sucralose can be neutralized by a treatment to convert any residual methoxide present to methanol. Conventionally this is accomplished by the addition of an [H+] ion exchange resin. Suitable ion exchange resins are known in the art and include AMBERLITE® IRC50 [H+] (Rohm and Haas).
  • any residual volatile solvents or reaction products are removed by distillation. Preferably this distillation is carried out under reduced pressure.
  • the reaction mixture is maintained at a temperature sufficient to keep the sucralose in solution. Generally the temperature will be from about 45° C. to about 50° C.
  • the sucralose containing solution Before or after the neutralization of the sucralose containing solution, it may be contacted with a decolorizing agent.
  • the decolorizing agent will be an activated carbon, but other decolorization agents can also be used.
  • the carbon may be in a powder form or packed in a column. However, the carbon must be removed from the solution before crystallization. The amount of carbon used will depend on the amount of colorant in the reaction mixture and the type of carbon. Those skilled in the art can readily determine the minimum appropriate amount of carbon to add to decolorize the mixture.
  • the carbon can be removed by conventional means (e.g. by filtration) if added in a loose form.
  • the buffer can be any food acceptable salts of food acceptable weak acids such as sodium or potassium acetate, citrate, ascorbate, benzoate, caprylate, diacetate, fumarate, gluconate, lactate, phosphate, sorbate, tartrate and mixtures thereof.
  • Preferred buffer include sodium acetate and sodium citrate which can be used. In fact minute amounts of sodium acetate may be present as byproduct reactions insufficient to buffer the crystallization.
  • the neutralization can be accomplished using any pH adjusting acid or base compounds that will not be inconsistent with the use of sucralose in food or compromise the taste of the final sucralose product.
  • pH adjusting compounds may be used sodium, potassium, or other food acceptable salts of hydroxide, carbonate, bicarbonate acetate, citrate, ascorbate, benzoate, caprylate, diacetate, fumarate, gluconate, lactate, phosphate, sorbate, tartrate and mixtures thereof.
  • a preferred pH-adjusting compound is sodium hydroxide.
  • the pH of the sucralose containing solution should be maintained in the range of about 5.5 to about 8.5 and preferably about 6.5 to about 7.8 and most preferably about 7 to about 7.8. Maintaining the pH in these ranges significantly enhances the long-term stability of the sucralose product and the recycled mother liquors.
  • the sucralose may be crystallized from the sucralose containing solution using conventional crystallization equipment.
  • the aqueous sucralose solution is concentrated to about 55 percent by weight sucralose content the sucralose and is cooled to between about 10° C. to about 30° C. and preferably between about 20° C. to about 25° C.
  • the aqueous sucralose solution is seeded with sucralose seed.
  • seed crystals comprising about 2 percent by weight of the sucralose in the crystallization mixture appear to provide desirable crystal formation.
  • the crystals are separated from the mother liquor using a centrifuge or filter and the mother liquor is recycled to an earlier point in the process after neutralization and before crystallization.
  • the mother liquor will be recycled and added to the reaction mixture after neutralization and before the decolorizing step.
  • the crystals may be washed to remove any residual mother liquor and dried using conventional drying equipment such as a tray or compartment dryer, agitated tray vertical turbo dyer, agitated batch rotary dryer, fluidized bed dryer or pneumatic conveying dryer.
  • the dryer can be operated at atmospheric pressure or reduced pressure in batch or continuous modes.
  • sucralose stability is enhanced if the residual sucralose moisture content is in the range of about 0.5 to about 10 percent by weight and preferably from about 0.5 to about 5 percent by weight and most preferably from about 0.5 to about 2 weight percent.
  • the sucralose referred to in this paragraph is non-hydrous meaning it does not contain any significant amounts of sucralose hydrates (e.g. sucralose pentahydrate). If the sucralose is dried to a lower moisture content the sucralose is actually less stable.
  • the temperature in the dryer should be held below 60° C. and preferably in the range of about 35° C. to about 45° C.
  • the moisture content of the final sucralose product will be maintained during shipping and handling between about 0.5 to about 10 percent by weight using a package that maintains the moisture content. The less permeable the material is the more moisture will be retained and the more stable the product will be.
  • the packaging will be a container that will maintain the moisture content of the sucralose. It is desired that the container have a moisture vapor transfer rate (MVTR) of not more than 0.25 gram water/100 square inches of surface area/24 hours, when tested at 38° C. at 92 percent relative humidity.
  • MVTR of the container will be not more than 0.2 grams/100 square inches/24 hours. More preferably the MVTR of the container will be not more than 0.15 grams/100 square inches/24 hours.
  • the packaging can be flexible or rigid packaging.
  • Suitable materials for making sucralose Packaging include but are not limited to moisture limiting packaging such as metallized or aluminum foil laminated substrates such as a polymer films or a kraft paper.
  • Suitable polymers include but are not limited to polyolefins (such as high-density (linear) polyethylene, polypropylene, etc.), polyesters (such as polyalkyl terephthalates e.g.
  • packaging materials that can be used including but not limited to multi-walled paper bags having a suitable moisture barrier, fiber drums having polymeric or aluminum foil linings integral with the drum wall or loose liners inserts. Rigid containers such as blow molded drums and pails made of polymers with moisture barriers may also be used. Flexible packages such as shipping bags made of a polymer substrate are preferred. Most preferred are bags made from aluminum foil laminated to polymer films formed from polymers that are commonly used to make moisture resistant packaging (e.g. laminates of aluminum foil and the polyolefins or polyesters listed above).
  • the pH stability test is conducted on the sucralose at time zero (the day the samples are placed in the oven, before the sucralose is exposed to elevated temperature) and every 24 hours until the batch being tested fails the test.
  • the sample fails the test if there is a pH drop of 1.0 pH unit or more.
  • the pH stability of the batch is defined as the number of days until the pH drop between the sample solution and that of the pH adjusted water is ⁇ 1.0.
  • the color stability of the batch is defined as the number of days until the first color development is observed.
  • sucralose A number of batches of sucralose were prepared with varying amounts of sodium acetate in the mother liquor and tested as above.
  • the optimum level of sodium acetate in solution during the crystallization of sucralose is 35-50 ppm. This level proved to be sufficient to maintain the pH during the crystallization at acceptable levels.
  • the stability of the final product was excellent and there was no acetic acid odor in the product.
  • the pH of the mother liquor has a tendency to drop over time. Historically, the pH has ranged from about 3 to about 4. We have now found that if the pH is adjusted to near neutral during crystallization, the stability of the final product is significantly enhanced. The following table records the stability results of several batches where pH during crystallization was varied.
  • impermeable packaging capable of retaining the moisture in the bag we were able to increase the stability of sucralose from 4 days to 33 days in accelerated stability testing. There is a direct correlation between the bag moisture permeability and product stability. It is clear that other moisture impermeable materials may be used to package sucralose and achieve this improved stability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Packages (AREA)
  • Saccharide Compounds (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US09/991,123 2000-11-17 2001-11-16 Sucralose composition and process for its preparation Expired - Lifetime US6646121B2 (en)

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US09/991,123 US6646121B2 (en) 2000-11-17 2001-11-16 Sucralose composition and process for its preparation
US10/632,876 US6809198B2 (en) 2000-11-17 2003-08-01 Sucralose composition and process for its preparation
US10/919,656 US20050013922A1 (en) 2000-11-17 2004-08-17 Sucralose composition
US11/522,566 US8017767B2 (en) 2000-11-17 2006-09-18 Sucralose composition

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US24978200P 2000-11-17 2000-11-17
US09/991,123 US6646121B2 (en) 2000-11-17 2001-11-16 Sucralose composition and process for its preparation

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US10/632,876 Expired - Lifetime US6809198B2 (en) 2000-11-17 2003-08-01 Sucralose composition and process for its preparation
US10/919,656 Abandoned US20050013922A1 (en) 2000-11-17 2004-08-17 Sucralose composition
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US11/522,566 Expired - Fee Related US8017767B2 (en) 2000-11-17 2006-09-18 Sucralose composition

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EP (1) EP1339728B1 (ru)
JP (2) JP4560637B2 (ru)
KR (1) KR100854528B1 (ru)
CN (1) CN1294139C (ru)
AU (2) AU2691802A (ru)
BR (1) BR0115482B1 (ru)
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US20040258822A1 (en) * 2003-06-16 2004-12-23 Shyhyuan Liao Chilsonated sucralose product
US20060210698A1 (en) * 2005-03-18 2006-09-21 Nehmer Warren L Granular sucralose
US20060247180A1 (en) * 2005-04-29 2006-11-02 Bergey James L Purgative composition and uses thereof
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US20070137157A1 (en) * 2005-12-19 2007-06-21 Mann & Hummel Gmbh Filter
US20070264403A1 (en) * 2006-05-11 2007-11-15 Nehmer Warren L Sparkling agglomerated sweetener, and method of making it
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US20090259036A1 (en) * 2008-04-03 2009-10-15 Tate & Lyle Technology Limited Extraction of less polar impurities from sucralose containing aqueous feed streams
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